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By Frederik. I write about money and the search for a meaningful life.
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The Moment that Made Louis C.K.'s Career

2024-11-10 06:52:54

I’ve been having some wonderful reader conversations recently. One question that comes up reliably is the direction of my work which I would charitably describe as “all over the place.” It reflects my wrestling with how my life has changed, as well as the push and pull between different inner voices, a back and forth between the comfort of the known and fear of the novel.

One reader reminded me of the time when Louis C.K. shared his story at the funeral of his hero, George Carlin. C.K. talked about the darkest point of his career. I had watched it years ago but it’s so honest and raw, that it immediately sent chills down my spine again (I shared the clip on Twitter).

I remembered the technique C.K. used to unlock his creativity. But just like the message of True Detective completely changed when I re-watched it this year, I realized that I had missed the change in C.K.’s mindset which unlocked his career.

C.K. began doing stand-up right out of high school. Even though he initially bombed on stage, he kept going and learned how to write decent jokes. “I wanted it so badly that I kept trying,” he said. But where did persistence lead him? He spent fifteen years perfecting his hour-long routine. Then he realized that he had gone in circles. He hated the act he had crafted so carefully.

Also, he was not successful. “I was working places like Chinese restaurants,” he recalled. “I’d do a show in a Chinese restaurant where they don't even know there's a show gonna happen. They're there to eat.”

“Nobody gave a shit who I was, and I didn't either.”

But fifteen years is a lot of sunk cost. What else was he going to do? “Stopping now is like getting out of prison. What do you do after 15 years of stand-up comedy?” Oof. Needless to say, C.K. was in “a dark place.” But fear kept him going.

Carlin on the other hand released a special every year and “each one was deeper than the next.” C.K. admired it but it also made him despair. “I just thought, how can he do that? And it made me literally cry that I could never do that.” How could he do that?

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Al Pacino and the Weight of Wealth

2024-11-07 05:31:19

In 2011, Al Pacino went broke. “I had fifty million dollars,” he writes in his new memoir Sonny Boy, “and then I had nothing.”

Pacino grew up poor in the Bronx. Life before making it as an actor was rough. “I tried it as a busboy and I didn’t make it,” he remembers. “They caught me eating off the leftovers from the tables. That’s how hungry I was.”

With that kind of childhood, I would have expected him to be extremely cautious and conservative with his money. I would have assumed he would avoid losing his money at all costs. Instead, he went broke twice.

The second time he was 70 years old, and the comeback was difficult. That’s when he joined Adam Sandler to make Jack and Jill which has a 3.3 score on IMDB. That must have been a difficult movie to make for an actor who adores Shakespeare and calls Chekhov his savior. “I never got into doing acting for money,” Pacino writes. “Except when I went broke. Then I got into it.”

“My life was costing me a fortune,” he writes, “my staff was getting bigger, and I was taking care of two homes, my apartments, and an office, and supporting the households of my children. I was spending three or four hundred thousand dollars a month…”

So what, you may ask? We know that’s not smart. Well, even he knew that. And yet he did it, twice. What he did is not as interesting as why he may have done it.

Pacino made it to the third money reality, abundance, and his memoir is filled with ambivalence about it. At times, I wondered if his wealth felt like a weight, whether a part of him rejected it.

“I've known very bright people that do not have money minds,” Warren Buffett once said, “and they can make very unintelligent decisions.” We don’t get to choose what kind of “money mind” we have. I used to think education was key. The more you learn, the more you wire your mind for success. But people like Pacino and Leonard Cohen had access to the best resources and advice, yet they went full circle.

I believe we all carry a collection of unconscious ‘money baggage,’ like a boulder. This weight makes the journey more difficult. It may block our sight or get in the way. It could even, as happened to Pacino, overwhelm us at a time of weakness and drag us back down in a tragic act of self-defeat.

Of course, this is an exercise in speculation. I don’t know what really went on in Al Pacino’s head. I suspect he doesn’t know either. The mind is too complex and memory plays tricks on us. Even so, his book offers a unique glimpse at how issues of mindset, identity, insecurity, and guilt can shape the relationship to money.

Let’s start with Pacino’s tone of helplessness. “Somehow I had managed to go broke,” he writes. “I could say I got taken advantage of. I could blame my accountants. I could blame Marty Bregman, who had put me into some sort of tax shelter that went south. I could blame myself, but then I’d have to take responsibility for my own actions.

That’s a theme throughout the book. He reflects on bad money behavior with a kind of shrug. The first time he went broke, Diane Keaton confronted his lawyer.

She was practically grabbing him by the lapels: “No, tell me who he is.” He started to speak, but Diane jumped in again: “Yeah, you’re going to tell me, ‘Oh, he’s an artist.’ No. He. Is. An idiot.”

I just stood there. What could I say?

Diane went on: “He’s an ignoramus. When it comes to this, you’ve got to take care of him.”

And he just… agreed. “She was right. I didn’t understand how money worked, any more than I understood how a career worked. It was a language I just didn’t speak.

When it came to business, he needed to be taken care of (Fredo in The Godfather comes to mind…). I think this defeatist mindset was formed in the poverty of his childhood:

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René Girard and the Port Strike Revelation

2024-10-27 01:49:14

Do you remember when a few weeks ago the port workers went on strike? Perhaps the event has already been swallowed by the election news cycle. But I remember. I remember that moment’s kernel of revelation.

I’m not talking about the uncomfortable truth that America’s ports are awfully inefficient, particularly compared to Chinese ones. I’m talking about the glimpse behind the curtain of our culture. For a few days, it felt like we were revealed to be characters in René Girard’s Theater of Envy.

It all started because union boss Harold Daggett apparently never read Peter Thiel’s Zero to One.

Daggett lives in a very nice house and the members of his union get paid very well. In fact, many get paid not to work thanks to a previous effort to block innovation in the form of shipping containers. But nobody cared until Daggett violated the first rule of rent-seeking: you do not talk about the racket.

Fight Club | Fight Club Wiki | Fandom
ready to choke a port

“All happy companies are different: each one earns a monopoly by solving a unique problem. All failed companies are the same: they failed to escape competition.” — Zero to One.

“Every great business,” Thiel wrote, “is built around a secret.” That secret is a way of avoiding competition and it is in the company’s best interest to carefully conceal it from competitors and regulators. Daggett did the opposite. “I’ll cripple ya,” he told the nation. “And you have no idea what that means.”

It was like that scene in Goodfellas when after the Lufthansa heist, gangsters buy fur coats and Cadillacs. Jimmy Conway loses his mind when he realizes that his crew will attract attention. Soon after, people show up in body bags.

Competition makes capitalism effective, yet successful capitalists avoid it. Investors are quite comfortable with this paradox. They recognize that finding moats is a profitable riddle (see for example a new paper by Michael Mauboussin). In other words, if Google lacks competition, add it to your portfolio. But if a union uses its power to extract a payoff, it sparks conflict (I read Daggett was shocked by the blowback and even received death threats).

I think there is more to it than the fact that they are on opposite sides of innovation. I think it is an issue of distance — what René Girard, leaning on Shakespeare, called a ‘Crisis of Degree’.

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☕📱Let's Chat on Zoom; Talent vs. Endurance: Haruki Murakami and Leonard Cohen

2024-10-22 02:03:37

Hello everyone,

Earlier this year, I offered readers a chance to get together over coffee. I took a break from all meetings over the summer but now feels like the right time to get back into conversations. I’ve dedicated a weekly time slot to these zoom calls. The process is straightforward: I’m adding a link at the end of this email to a simple form (name, email, and some questions to ponder). I will check the responses every week and send respondents an email with a Calendly link.

I look forward to chatting with you all!


There are several reasons why Leonard Cohen’s story touched and inspired me. My natural tendency in the face of problems is to retreat and isolate. Cohen’s story reminded me that sharing is a better response. Each time he faced money issues, he stepped up his game.

Cohen also was also considered too old when he began to make music and he sustained a long creative career. I wrestle with the idea of age all the time. I don’t feel like I’m in my late thirties. In some ways, I feel younger and more curious than in my twenties. But I don’t kid myself either. It’s difficult to learn new skills and explore new paths later in life. One reason is simply that our energy declines. Haruki Murakami wrote about this in his wonderful little meditation What I Talk About When I Talk About Running.

To Murakami, the three key qualities of a good novelist were talent, focus, and endurance. Talent is unevenly distributed meaning that “life is basically unfair.” He also observed that many writers, even very talented ones, experienced a painful creative burnout and decline as they aged. At first talent would carry them. But eventually, the well would be dry and they had not learned how to dig for new sources of water. “To deal with something unhealthy,” he wrote about writing and making art, “a person needs to be as healthy as possible. That’s my motto. In other words, an unhealthy soul requires a healthy body.”

Murakami felt he didn’t have as much talent as others and his response was to “seek out a kind of fairness” by doubling down on process. He would excel with endurance and focus — and his career would be long. Running became his source of energy. The persistence and practice required for marathons would be the foundation of his writing.

Writing novels, to me, is basically a kind of manual labor. Writing itself is mental labor, but finishing an entire book is closer to manual labor. … The whole process—sitting at your desk, focusing your mind like a laser beam, imagining something out of a blank horizon, creating a story, selecting the right words, one by one, keeping the whole flow of the story on track—requires far more energy, over a long period, than most people ever imagine. … for the novelist that process requires putting into play all your physical reserve, often to the point of overexertion.

I’ve been thinking about Murakami’s words a lot.

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Setbacks are Inevitable, Defeat is Optional: The Strength of Leonard Cohen

2024-10-15 23:26:58

Leonard Cohen didn’t record his first album until he was thirty-three. It was 1967 and by the standards of the hippie era (“Don't trust anyone over 30.”), he was late to the game. “A thirty-two-year-old poet? Are you crazy?” one record label executive said when Cohen was signed.

I just finished the Cohen biography I’m Your Man and a heartwarming documentary about the origins of Hallelujah, his best-known song (famously covered by Jeff Buckley and many others).

I was struck by a particular aspect of Cohen’s story: his resilience.

You see, by ‘67 Cohen was already an award-winning poet and novelist. The free-spirited bohemian had moved from Montreal to the Greek island of Hydra. There was only one issue: money.

Hydra was cheap, but not cheap enough. “I couldn’t pay my grocery bill,” Cohen explained, “so I would come back to Canada, get various jobs, get that money together plus the boat fare, come back to Greece, and live for as long as that money lasted.”

At a time when people were still reading, Cohen still “couldn’t make a living as an author.” How easy would it have been for him to throw up his hands in resentment and abandon his art. Wasn’t the world telling him that what he did was not valuable enough? Instead, he picked up his guitar and turned poems into songs.

Now let’s fast forward about forty years…

When Cohen’s long-time manager passed away in the 1980s, his assistant Kelley Lynch took over management of Cohen’s affairs. Cohen and Kelly had a brief “casual sexual arrangement” but remained friends and Cohen kept her as his new manager. Artists, am I right? In any event, in the 1990s Cohen spent six years at a Zen monastery. He gave Lynch broad power of attorney over his financial affairs.

In 2004, Cohen’s daughter was warned about Lynch. When Cohen reviewed his accounts, he found that Lynch had been taking money. One of the first things he noticed was a personal American Express bill of $75,000 that Lynch had paid out of Cohen’s accounts. After months of work, his lawyer estimated that “between ten and thirteen million dollars had been improperly taken.”

Cohen was 70 years old. One day, as he put it, he “walked to the ATM” and his money was gone.

It seems to me there were two ways he could have responded.

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